


Earn Your Second Chance

by CynicalLion



Category: Borderlands (Video Games)
Genre: Breathplay, Daddy Kink, Degradation, Dubious Consent, Grinding, Hair-pulling, Humiliation, M/M, Masochism, Oral Sex, Overstimulation, Painful Sex, Sadism, Shoe Grinding, Strangulation
Language: English
Status: Completed
Published: 2021-01-31
Updated: 2021-01-31
Packaged: 2021-03-17 16:33:45
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,292
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29103363
Author URL: https://archiveofourown.org/users/CynicalLion/pseuds/CynicalLion
Summary: Timothy makes a mistake that makes Jack just mad enough to decide he doesn't really need him around. When trying to strangle Timothy ends up being less effective than Jack had anticipated, he decides on a different way his body double can pay for his screw-up.
Relationships: Handsome Jack/Timothy Lawrence
Kudos: 34





	Earn Your Second Chance

**Author's Note:**

> I was trying to make my friend suffer with gay feelings for Handsome Jack since we both think he's just... the best, and I ended up liking what I wrote enough to make something out of it. Goes to show why I shouldn't try to tease people! I usually end up liking it myself!

"See, when I got the report, I didn't quite believe it, so I'd like to hear what happened from you." Handsome Jack was sitting at his desk, all of his monitors pushed aside as he glared at his favorite body double. His soon-to-be very, **very** dead favorite body double.

Shrinking into his seat across from Jack, Timothy swallowed hard. "We-- **I** lost the shipment, sir." He said quietly, glancing up and flinching at the irritable frown on Jack's face. "The Crimson Raiders and Vault Hunters ambushed it and--" Timothy instantly shut up when Jack sighed and stood.

"Yeah, I read the report." Jack said, placing his hands on his desk to lean over it a bit and glare at Timothy. "Thing is, I didn't like hearing it from you any more than I liked reading it for myself." Straightening up again, Jack began to make his way slowly around the desk, watching as Timothy timidly rose from his seat but made the mistake of facing him, which trapped him with his back to the massive desk now behind him. "So that's a problem. A friggin' **big** problem considering that shipment that you lost was worth more than it took to create your sorry ass."

"Sir, Jack, pl-please, I--" Timothy started, breaking off in a gasp as he backed up into the desk in an attempt to escape Jack's slow, predatory advance on him. "I-I can get the shipment back!" He shouted, putting his hands up as Jack officially cornered him.

"See, I'd let you try, Tim, I would, but considering this whole thing is _your_ fault to begin with," Jack paused, giving a humorless laugh, "you can see why that feels _suuuper_ counter-productive, right?"

"No, please--!" Timothy yelped as Jack lunged at him, not getting out anything more as Jack's large hands wrapped tightly around his throat. He instantly went to Jack's wrists, trying to pull him off, but Jack was stronger and didn't even seem to notice Timothy's efforts.

"It's a real shame, too." Jack growled, tightening his hold, his upper lip quirking up into a sneer as Timothy added his blunt nails to his struggling. "I actually liked you a little." Tears sprung to Timothy's eyes and his face began to turn red and Jack couldn't help but marvel at how _good_ he looked like this. It made sense, when Jack thought about it. Timothy looked like himself, after all, and he looked good no matter what he was doing, so of course he even looked good getting strangled.

Timothy's clawing became more desperate and he started to squirm so Jack stepped forward with the full intention to bear down on him and keep him still. When his leg slotted between Timothy's, though, he found something he hadn't been expecting and had to look down to make sure he wasn't mistaken. Timothy let out a desperate, breathless sound as Jack looked down but that didn't stop him from seeing the clear and obvious erection straining against his zipper.

"Well, well, well." Jack breathed, looking back to Timothy's cherry red, tear-streaked face and grinning toothily. "I didn't know you were into shit like this, Timmy." He teased, loosening his grip and feeling the bob of Timothy's Adam's apple as he gulped down desperate breaths.

"I'm not, I--" Timothy started, getting cut off by Jack's hands again as he tightened them once more.

"Ah, ah, ah, Timmy, you shouldn't lie to your boss. Especially not since I've got pretty solid evidence to the contrary here." Jack scolded, pressing his leg firmly into Timothy's crotch and laughing in surprise when his hips bucked against his leg. "You know what? I think you might be enjoying your punishment a little too much." He said quietly, like it was a secret or a scandalous bit of gossip.

"I'm sorry, sir, I--" Timothy tried as Jack loosened his grip, his desperate attempts to speak getting cut off by an equally desperate moan when Jack shifted his leg against his straining erection.

"Y'know, I'm still pretty pissed about that shipment, but I think I can work with this." Jack hummed, giving Timothy's neck one last hard squeeze just to make super sure he'd bruise before letting the crying man go. "On your knees, kitten. I just thought of a way you can try to earn that chance to get the shipment back."

Eyes widening as his odds of getting strangled to death suddenly decreased from one-hundred percent, Timothy quickly dropped to his knees. The new angle gave him the perfect view of the semi Jack was packing and it only made his light trembling kick up a notch to see the obvious proof of how much Jack enjoyed hurting him. He looked up nervously at Jack and swallowed despite his aching throat at the cruel spark in his mismatched eyes. He wasn't going to like whatever was about to save his life. He could guess what it would be given his new position, but he was desperately hoping he was wrong. It wouldn't be the first time Jack had demanded a blow-job, not even close, but it would be the first time Timothy had to start with his throat already sore as hell.

"God damn, I even look good like this." Jack said, shaking his head as his eyes roamed Timothy's pathetic face appreciatively. Then his face suddenly hardened and he raised an impatient eyebrow at Timothy. "Well? Chop chop, princess, the less fun I have while you're on your knees, the less likely you are to leave this office still breathing."

Jolting as if electrocuted, Timothy quickly reached forward with his slightly shaky hands and freed Jack from his beat-up jeans and bright yellow Hyperion brand boxers. Normally the stupidly bright boxers with their dorky little "H"s would be enough to at least get a half-smile from Timothy, but he didn't have the luxury currently. Currently, he needed to make sure Jack didn't go back to strangling him. With that objective in mind, Timothy grabbed the base of Jack's intimidating dick and took the head into his mouth.

Jack was a man who enjoyed foreplay. For as impatient as he could be in other aspects of his life, if he had the time, he liked to make sex last. Timothy knew this wasn't one of those occasions. This wasn't just a casual office blow-job, this was a life or death evaluation and he _needed_ to pass. Pressing the tip of his tongue firmly into the slit of Jack's dick, Timothy moved it up and down for a few strokes and then swirled his tongue slowly around the whole head, making sure not to miss a single centimeter in his rotation.

As Jack groaned lowly at the attention, Timothy slowly moved his head down to take him as far as he could before Jack's cock bumped the back of his aching throat. He knew Jack would get impatient eventually and force him to take him all the way down, but for now, he was going to try his damnedest to spare his throat the extra pain. For now, this was actually sort of nice.

Timothy would be lying if he said he didn't enjoy this normally. He liked blowing Jack, even when Jack got a little rough with him. Despite his pain and fear, it appeared his body remembered how much he usually enjoyed this, because his embarrassing, potentially life-saving boner hadn't gone down yet. In fact, it was starting to get painful. Shifting his hips a bit to try and relieve some pressure, Timothy pulled up on Jack's cock, running his tongue along the underside the entire way up and sucking pointedly on the head once he made it there.

Groaning again, Jack ran his hand roughly through Timothy's hair, stopping at the half-way point and pulling. Timothy came off his cock with a soft yelp and Jack looked down at his flushed face, smirking at the slightly glazed-over look of his eyes. "Still enjoying yourself, Timmy? For shame." He teased, pulling Timothy back onto his cock when he opened his mouth, likely to apologize, and making him take it all this time. Timothy gagged and let out the best whine he could given his state, but got with the program quickly and started to suck.

"Atta boy, TimTam." Jack breathed, starting to slowly move Timothy's head up and down his cock at a leisurely pace. "Maybe it wasn't your fault that shipment got stolen, huh? Maybe that was on me. I mean, clearly **this** is where you're _meant_ to be. On your knees choking on cock, not out in the field doing big boy work." Jack teased, grinning when Timothy flinched at his assessment. "Oh, don't pretend you wouldn't love that, pumpkin." He growled, pulling Timothy off his cock and glaring down at him. "A life on your knees, no responsibilities except taking what I give you, no more danger except the risk of ticking me off."

Despite himself, Timothy whined softly, his pants growing ever tighter. That did sound good, it sounded so good. God, he was tired of getting shot at and he was so good at making Jack happy with his body. As though he could read his thoughts, and hell, for all Timothy knew, he could, Jack carried on. "And how could you mess up such a simple job?" He asked, loosening his grip on Timothy's hair to stroke it gently. "You're so good at following orders and taking a cock, even you couldn't screw up a job like that."

As Timothy whimpered, his eyes closed and his hips twitching occasionally in a futile attempt to find some friction, Jack couldn't help but grin mockingly. "Pathetic." He hissed, chuckling when Timothy flinched and looked at him for only a second with the most betrayed expression before turning his gaze away. "Open wide, you pathetic little cock-slut." And, proving Jack's point about his ability to follow orders, Timothy did, his mouth dropping open obediently.

"Good boy." Jack purred, taking Timothy's head in both hands and forcing him to take his cock to the root slow enough that Timothy winced but didn't gag as it entered his throat. "Now, make Daddy happy or I'm gonna paint your face with cum and send you out the airlock so everyone on Helios can watch your stupid, cum-covered corpse float on by and get a chuckle out of it." He threatened calmly, letting Timothy's head go and watching the discomfort on his face as he started to bob his head, taking Jack to the root every time.

When Timothy started to suck and add a swipe of his tongue across the head of Jack's cock with every bob, Jack groaned lowly and tipped his head back. "Such a good little cock-sucker." He huffed, sliding his foot forward and pressing the bottom of his shoe against Timothy's straining erection. Timothy jolted and moaned in surprise, the vibration causing Jack to grunt and buck his hips. "Gonna make you jizz in your pants like the pathetic little waste of space you are." Jack growled, pressing his foot harder into Timothy's crotch and groaning when he moaned and bobbed his head faster. "You like that, huh? You wanna cum in your pants, TimTam?"

"Yes, Daddy." Timothy practically whispered, shuddering as a jolt of pleasure raced up his spine when he glanced up and saw the dark arousal in Jack's eyes.

"Say that again." Jack demanded lowly, sincerely considering sparing Timothy once this was all over for the first time since this had all started.

"Please make me cum in my pants, Daddy." Timothy said softly, veering a little off-script considering Jack's command but feeling he'd made the right decision to do so when Jack bared his teeth in what could almost be considered a grin and tangled a hand in his hair again.

"How's something so worthless so friggin' sexy?" Jack asked lowly, forcing Timothy's head forward again by his hair and then letting Timothy take over again. While Timothy blew him like his life depended on it, appropriately enough, Jack ground his foot slow and hard into his crotch. The pressure had to be painful, but Timothy's hips kept twitching up into it and even as his eyes prickled with tears, he was moaning around his cock, so he was clearly enjoying the pain.

When Jack accidentally added too much pressure to his grinding due to Timothy's distracting tongue, Timothy accidentally bit him and that's what finally sent Jack over. He let out a few choice swear words and held Timothy's head to his crotch, forcing him to swallow the full load. Jack felt Timothy shaking but he didn't pay him any mind until he'd finished cumming. Finally pulling Timothy's head back, Jack looked down at him and realized he was trying to escape his foot, having apparently cum while Jack was forcing him to take his load.

"Aw, what's wrong, Timmy? Too sensitive?" Jack cooed mockingly, getting a whimper for his efforts and chuckling. "Use your words, TimTam."

"Yes." Timothy whined, still trying to shy away from Jack's insistent foot without outright pulling away from him. "Please, sir."

Humming in pretend thought as he tucked his cock away, Jack let Timothy suffer a bit more before finally releasing his hair and taking a step back. "Congratulations, cupcake, you bought yourself twenty-four hours to fix your screw-up." He declared, smirking when Timothy looked up at him with clear protest written across his face. "Starting now." Jack added, his tone making it clear that he wouldn't be budging on this.

Deflating a bit, Timothy nodded, looking away from Jack's smug face. "Thank you, sir. I won't let you down this time."

"You'd better not, sweetheart. You'd better not."


End file.
